Chloroethyl chloboethoxt-e jl mtlj



Patented Dot. 15, 1935 UNITED STATES PATENT OFFICE CHLOROETHYL CHLOROE'I'HOXY-ETHYL ETHER Henry L. Cox, South Charleston, W. Va... assignor to Carbide and Carbon ChemioalsConioration, a oorporationnf New York No Drawing. Application April 1'1, 1934,

Serial No. 720,947

3Clalms.

adapt it admirably for use in the production oflubricants. Particularly, it may be substituted I for dichloroethyl ether and like solvents in lubricants for use in high-pressure lubrication, or wherever undue voiatilization of the lower boiling dichloroethyl ether would eilect a breaking 1B of the film of lubricant. The new ether is also adapted for use in organic synthesis, and as a high-boiling,- chlorinated solvent and extractant, being a good solvent for oils and for hydrocarbons. The compound appears to have a structure corresponding to the formula:

CICmCm-Q-Cm-MCHQCL and may also be identified as p-chloroethyl pchloroethoxy-ethyl ether, or as triethylene glycol 2 dichloride.

The new compound may be prepared by reacting ethylene chlorhydrin or ethylene oxide with chlorine and ethylene, preferably in the presence of water and attemperatures in the range from around atmospherictemperature. 20

0., to aroimd 100 C. Waterfchlorine and ethylenemaybeusedasstartingmaterials,inwhich momonpo-em-omonom. oloniom-o-om-o case ethylene chlorhydrin is continuously formed from the water and a part of' the chlorine and oleflne.

In the practice ofthe invention according to one modification thereof, ethylene and chlorine are bubbled through a body of water in a closed chamber. The gases are introduced into the chamber in uniform manner by means of the,

Ethylene oxide is also passed usual diffusers. through the body of liquid at such a rate as to react with most. of the free acid and thus maintain the liquid slightly acid. The water, chlorine,

and ethylene react to form ethylene chlorhydrin and hydrochloric acid, and most of the latterreacts with the ethylene oxide to form additional ethylene chlorhydrin. The unexhausted gases may be recycled in the process in the interests of economy. The chloroethyl p chloroethoxy 5 ethyl ether and byproducts concurrentlyformedgradually accumulate in the liquid body. Water a is added occasionally to prevent depletion ofthe chlorhydrin content of the liquid. When the accumulated products are present in suilicient 1o amount (they often form nearly half of the liquid contents) all or a portion of the liquid may be treated with water. Upon standing, two layers form, the upper one of which may be returned for further treatment in the manner described to above. The lower layer contains the new ether together with water and some chlorhydrin and other products. Washing the layer with water removes a part of the chlorhydrin. The remaining liquid is then subjected to fractional distllla- 20 tion, preferably under subatmospheric pressure, and the fraction distilling over at around 118 C.

at 10 mm. pressure contains the p-chloroethyl p-chloroethoxy-ethyl ether. The flnal puriflca tion of the latter is accomplished by distillation 25 under suba'tmospheric pressure.

The reactions which probably occur in the production of the new ether are indicated in the following equations. It will be understood, however, that the invention is not in any sense to be 30 considered as limited by any statement of theory appearing herein.

m-o-bmomoi fi-chloroethory ethyl B-chloroethyl other The p-chioroethyl p-chloroethoxy-ethyl ether may he recovered from the resultant reaction mixture by fractional distillation, preferably under subatmospheric pressure, either with or without a prior separation therefrom of an aqueous layer containing the chloroethanois for reuse in the process. 50

The invention is susceptible of modification within the scope of the appended claims.

I claim: k

1. As a chemical compound, p-chloroethyl-fichloroethoxy ethyl ether, the same being a liqg5 formula ClCHzCHz-O-CHzCHz-O-CHzCI-BCI.

3. As a new chemical compound, triethylene glycol dichloride, the same being a. water-insol- 5 uble high-boiling solvent for oils and hydrocarbons, and boiling at about 118 C. under 10 mm. of mercury absolute pressure.

HENRY L. COX. 

